Diisopropylamine → HCID 67155049, compound

Participants

Reaction Conditions

Reaction Steps

n-BuLi (1.6 M in hexane, 4.26 mL, 6.82 mmol) was added dropwise to a solution of diisopropylamine (1.05 mL, 7.39 mmol) in THF (14 mL) at −78° C. under Nitrogen atmosphere. The resulting mixture was warmed up to −40° C. and stirred for 10 min and recooled to −78° C. A solution of 3-bromo-5-fluoropyridine (1000 mg, 5.68 mmol) in THF (5 mL) was added dropwise at this temperature. After completion of addition, the reaction mixture turned brown. After 30 min, Oxetan-3-one (491 mg, 6.82 mmol) was added dropwise and the resulting mixture was stirred for 30 min at this temperature. The reaction was quenched with saturated NH4Cl solution. The mixture was extracted with ethyl acetate, and the combined extracts were washed with saturated NaHCO3 solution, dried over Na2SO4 and filtered. After concentration, 3-(3-Bromo-5-fluoro-pyridin-4-yl)-oxetan-3-ol (1190 mg, 84%) was obtained as a dark red solid; ESI-MS m/z: 249 [M+1]+, Retention time 0.83 min; 1H-NMR (MeOD, 400 MHz) δ 4.77 (d, J=8.8 Hz, 2H), 5.25 (d, J=8.8 Hz, 1H), 5.26 (d, J=8.8 Hz, 1H), 8.45 (d, J=1.6 Hz, 1H), 8.56 (s, 1H).

Provenance & Evidence